153-18-4 Usage
Uses
Used in Pharmaceutical Applications:
Rutin is used as a capillary protectant for strengthening and tightening skin capillaries, which may help prevent conditions like couperose. It also demonstrates antioxidant properties, making it a valuable component in the development of pharmaceutical products.
Used in Nutritional Products:
Rutin is used as a nutritional supplement due to its potential health benefits, such as its antioxidant properties and its ability to strengthen capillaries. It is often found in dietary supplements and health products.
Used in Antidiabetic Applications:
Rutin is used as a dipeptidyl peptidase-4 (DPP-4) inhibitor, which helps regulate blood sugar levels and may be beneficial for individuals with diabetes.
Used in Cosmetic Applications:
Rutin is used in the cosmetic industry for its skin-strengthening and capillary-protecting properties. It may be included in skincare products to help improve the appearance and health of the skin.
Used in Plant Sources:
Rutin is found in many plants, particularly the buckwheat plant, and is often extracted from these sources for use in various applications. Some common sources of rutin include rue leaves, buckwheat, and other plants from the Rutaceae, Sectaceae, and Polygonaceae families.
History
In the mid-1930s, Hungarian scientist Szent Gyorgy firstly separated the flavonoid
mixture. After the German pharmacy firstly made it into ranosine in 1942, the concept
of vitamin P has been established worldwide. Further study proved that rutin
was the most important flavonoids of vitamin P. These compounds were certified to
have effects on many diseases in medical.Recently, the research of rutin mainly focuses on the extraction process improvement,
pharmacological effects, and pharmacodynamics research, aiming at improvement
of its bioavailability through the development of different dosage forms. As
for the extraction process, new extraction and purification methods have been developed
since the original alkali extraction acid precipitation method. These methods
greatly improve its extraction efficiency and reduce cost, including hot water precipitation,
hot water extraction with macroporous resin adsorbing purification,
ultrasonic radiation, hot water extraction with alcohol precipitation, cold alkali percolation
extraction with acid precipitation, continuous reflux extraction, ethanol
extraction, supercritical CO2 extraction, and enzymatic hydrolysis .In recent years, advanced rutin dosage forms, such as rutin cyclodextrin saturation,
HPMC controlled release tablets, solid dispersion tablets, coprecipitate, and
rutin effervescent particles, greatly improve the rutin dissolution rate and its
bioavailability.
Pharmacology
As a flavonoid substance, rutin has a significant protective effect on the cardiovascular
system, including the endothelium-dependent vasodilation through
NO-guanylate cyclase pathway, antagonization on platelet-activating factor (PAF),
inhibition on subsequent reactions induced by PAF binding to its specific membrane
receptor, and protection of myocardial cells .Rutin also has good free radical scavenging effects. Studies showed that rutin
and its derivatives had a strong free radical scavenging effect, of which rutin possessed
the strongest antioxidant activity. Rutin removed superoxide anion and
hydroxyl radicals, exerted a strong anti-lipid peroxidation, protected mitochondria,
and enhanced the activity of superoxide dismutase (SOD).
Clinical Use
Rutin is mainly used for the adjuvant treatment of hypertension and treatment for
the prevention of other bleedings due to lack of rutin, such as cerebral hemorrhage,
retinal hemorrhage, purpura, acute hemorrhagic nephritis, chronic bronchitis, and
abnormal blood osmolality, restoration of capillary elastic embolism, and also for
the prevention and treatment of diabetes and hyperlipidemia . Troxerutin, the
most important active ingredient in hydroxy rutin, is used in the treatment of varicose
veins/venous disorders, hemorrhoids, lymphedema, and postoperative edema,
treatment of thrombosis and cerebrovascular disease, and also in the treatment of
diabetes and liver disease. Since rutin has a mild effect with low cost and less
adverse reactions, especially its remarkable effect on acute cerebral infarction, it is
of great worth on promotion and application of rutin .
Purification Methods
The vitamin crystallises from MeOH or water/EtOH, dry it in air, then dry it further for several hours at 110o or in high vacuum at 120o. It forms yellow crystals from EtOH/Me2CO/H2O (2:1:1). It has also been purified by passing (0.5g) through a Kieselgel column (30 x 5cm) with EtOAc/MeOH/H2O (100:20:15), and after 750mL have passed through, the yellow fraction of 250mL gives the glycoside (0.3g) on evaporation. [H.rhammer et al. Chem Ber 101 1183 1968, Marini-Bettòlo Gazz Chim Ital 80 631 1950, Beilstein 18/5 V 519.]
Check Digit Verification of cas no
The CAS Registry Mumber 153-18-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 3 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 153-18:
(5*1)+(4*5)+(3*3)+(2*1)+(1*8)=44
44 % 10 = 4
So 153-18-4 is a valid CAS Registry Number.
InChI:InChI=1/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8?,15?,17-,18+,20-,21+,22?,23?,26+,27-/m0/s1
153-18-4Relevant articles and documents
Labdane diterpenes and flavonoids from Leonurus japonicus
Seo, Hyun Kyu,Kim, Ju Sun,Kang, Sam Sik
, p. 2045 - 2051 (2010)
Chemical investigation of the aerial part of Leonurus japonicus led to the isolation and characterization of a new labdane-type diterpene, named 3α-acetoxy-15-O-methylleopersin C (3), and a new acylated rutin derivative, named 2?-syringylrutin (9), along with seven known compounds, including a labdane-type diterpene and six flavonoids. The structures of the new compounds were established by spectroscopic methods.
READILY WATER-SOLUBLE ISOQUERCITRIN COMPOSITION
-
, (2012/04/11)
Disclosed is a method for improving the solubility of isoquercitrin in water. Also disclosed is a readily water-soluble isoquercitrin composition which has improved solubility in water due to the method. Specifically disclosed is a method for preparing an isoquercitrin inclusion product, which comprises including isoquercitrin in γ-cyclodextrin in the proportion of 2 to 10 mol of γ-cyclodextrin to 1 mol of isoquercitrin.
Recovery of isoquercetin from bioflavanoid pastes
-
Page column 3-4, (2008/06/13)
The invention relates to a method for recovering high-purity isoquerectin from bioflavonoid pastes, that is from mother-liquor residues which are produced during the recovery of flavonoids, by extraction with a solvent mixture of methyl acetate and water.
Pharmaceutical compounds for treating copd
-
, (2008/06/13)
Use of an MPO inhibitor for the treatment of COPD.
Ume extract having medicinal effects and compositions containing the same
-
, (2008/06/13)
Extracts are prepared from a leaf and a stem of ume, a kernel of ume, and an ume flower, using methanol in an amount of 5 times the volume thereof. These extracts have anti-oxidation action, gastric mucosa injury inhibiting action, aldose reductase inhibiting action, blood glucose level elevation inhibiting action, platelet agglutination accelerating action, alcohol absorption inhibiting action, anti-inflammatory action, and the like.
Reduction potentials of flavonoid and model phenoxyl radicals. Which ring in flavonoids is responsible for antioxidant activity?
Jovanovic, Slobodan V.,Steenken, Steen,Hara, Yukihiko,Simic, Michael G.
, p. 2497 - 2504 (2007/10/03)
Model phenoxyl and more complex flavonoid radicals were generated by azide radical induced one-electron oxidation in aqueous solutions. Spectral, acid-base and redox properties of the radicals were investigated by the pulse radiolysis technique. The physicochemical characteristics of the flavonoid radicals closely match those of the ring with the lower reduction potential. In flavonoids which have a 3,5-dihydroxyanisole (catechins), or a 2,4-dihydroxyacetophenone (hesperidin, rutin, quercetin)-like A ring and a catechol- or 2-methoxyphenol-like B ring, the antioxidant active moiety is clearly the B ring [reduction potential difference between the model phenoxyls is ΔE(A-B ring models) > 0.1 V]. In galangin, where the B ring is unsubstituted phenyl, the antioxidant active moiety is the A ring. Even though the A ring is not a good electron donor, E7, > 0.8/NHE V, it can still scavenge alkyl peroxyl radicals, E7, = 1.06 V, and the Superoxide radical, E7 > 1.06 V. Quercetin is the best electron donor of all investigated flavonoids (measured E10.8 = 0.09 V, and calculated E7 = 0.33 V). The favourable electron-donating properties originate from the electron donating O-3 hydroxy group in the C ring, which is conjugated to the catechol (B ring) radical through the 2,3-double bond. The conjugation of the A and B rings is apparently minimal, amounting to less than 2.5% of the substituent effect in either direction. Thus, neglecting the acid-base equilibria of the A ring, and using those of the B ring and the measured values of the reduction potentials at pH 3,7 and 13.5, the pH dependence of the reduction potentials of the flavonoid radicals can be calculated. In neutral and slightly alkaline media (pH 7-9), all investigated flavonoids are inferior electron donors to ascorbate. Quercetin, E7 = 0.33 V, and gallocatechins, E7 = 0.43 V, can reduce vitamin E radicals (assuming the same reduction potential as Trolox C radicals, E7 = 0.48 V). Since all investigated flavonoid radicals have reduction potentials lower than E7 = 1.06 V of alkyl peroxyl radicals, the parent flavonoids qualify as chain-breaking antioxidants in any oxidation process mediated by these radicals.
A FLAVONOL TRIGLYCOSIDE FROM BACCHARIS THESIOIDES
Liu, Yong-Long,Timmermann, Barbara N.,Hoffmann, Joseoh J.,McLaughlin, Steven P.
, p. 1549 - 1551 (2007/10/02)
Five flavonols have been isolated from the aerial parts of Baccharis thesioides.On the basis of spectroscopic analysis the structure of a new flavonol triglycoside has been elucidated as quercetin 3-O-2)α-L-rhamnopyranosyl (1->6)>-β-D-glucopyranoside.Four known flavonols were identified as rutin, hyperoside, isoquercetin and quercetin.
